Hair setting composition containing a ring substituted n-vinyl-2-oxazolidinone polymer



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to rates HAIR SETTING COMPOSITION CONTAINING A RING SUBSTITUTED N-VlNYL-Z-OXAZOLIDI- NONE POLYMER No Drawing. Filed Jan. 28, 1958, Ser. No. 711,560 13 Claims. (Cl. 1'67--87.1)

The present invention has reference to a new and improved composition,. as well as to a process utilizingsuch composition, for setting hair on the human'head into a desired waveshape or dressed arrangement in order to effect a relatively transient or temporary alteration of the type that may be obtained with the so-called hair set formulations (as destinguished from permanent wave preparations).

The instant application is a continuation-in-part of the copending applictaion for United States Letters Patent of Wilhelm E. Walles, William F. Tousignant and Thomas Houtman, Jr., entitled X-Alkyl-N-Vinyl-Z-Oxazolidinone Compounds, having Serial No. 696,317, which was filed on November 14, 1957.

A considerable variety of materials and formulations have been employed for the temporary setting of human (and the like) hair. Among these there may be mentioned gums and other film-forming chemicals, such as water-soluble polymer or other plastic substances which tend to serve as stifieners for the hair to permit the achievement of better setting results than are obtained with simple water sets. The known formulations may be prepared as lacquers or solutions for direct application and use as liquids. They may also be made up for spray application from aerosol dispensers. Frequently, the applicating formulations may contain certain swelling agents and penetrating assistants elfective upon the hair as well as plasticizing ingredients for the hair setting and stiffening component. Assistants of the indicated variety oftentimes possibilitate deposition of the stiffening agent from the setting formulation both within and without the individual strands of the hair being set so as to achieve even better results.

The conventional and heretofore known formulations that are adapted to merely stiffen the hair by means of external sheath formation about its individual strands are sometimes dissatisfactory due to the general fragility and propensity to soften or crack of the deposited stiffening agent, or because of its inept behaviorism with respect to moisture. Thus, some of the stifiening agents are not sufficiently hygroscopic to be beneficially plasticized by the humidity in the air so as to permit them to have a desirable consequent softening influence on the dressed and set hair. Others may definitely deteriorate in the continued presence of moisture, or at least lose substantial portions of their elfectiveness under. conditions of high relative humidity in the air.

One of the currently most popular of the setting or stiffening components for hair is polyvinylpyrrrolidone (more properly, poly-N-vinylpyrrolidone or poly-N-vinyl- 2-pyrrolidone and, even more properly, poly-N-vinyl-2- pyrollidinone, hereinafter referred to as PVP) which may most advantageously be utilized in formulations comprised additionally of such swelling agents for human hair as triethanolamine and urea (or their equivalents), preferably in an aqueous carrier. 'The use of PVP in hair setting compositions is discussed in an article apatent for January 1956 (volume 34). Such compositions have also been disclosed and are described in United ,States Letters Patent Number 2,793,980.

While PVP is an excellent agent for hair setting formuw" lations (including those of the non-swelling varieties wherein it functions as a mere stiffening agent), it is not Without disadvantages and drawbacks. For example, it is sometimes difficult to obtain PVP as a commercial product of reliably consistent uniformity and quality. Furthermore, the exceptionally hygroscopic nature of PVP may hinder its hair setting efficacy under condi tions of high relative humidity. In addition, a serious disadvantage of PVP lies in the fact that certain batches of the polymer may at times cause hair sprays and other. hair setting formulations prepared therewith to have an objectionable odor, best described as a somewhat mousey smell, which may become associated with the. hair upon which the formulation is applied. The development of such odor (which, upon its occurrence, is a practical intolerability) is believed to be due to the formation of acetamide upon the degradation of the PVP;

The object of the present invention is to provide new and improved hair setting compositions and formulations, as well as processes for their utilization, capable of providing truly superior results without being subject to the drawbacks and deficiencies of the heretofore known materials for such purposes.

According to the present invention, superior hair setting compositions arecomprised essentially of a solvent carrier containing dispersed therein as a setting agent a ring substituted N-vinyl-2-oxazolidinone polymer, or a mixture of such polymers, of the general structure:

wherein each X is independently selected from the group consisting of hydrogen and alkyl radicals containing froni l to about 4 carbon atoms, particularly methyl and ethyl radicals, with the limitation that not more than three of said substituent members can be hydrogen, and n is a plural integer, preferably one whose numerical value is greater than about 10 and which maybe as large as 2,000-5,000 or more. Advantageously, a polymer is employed having a mono alkyl ring substituent in the 5- position, such as poly-N-vinyl 5 methyl-2-oxazolidinone (PVO-M) and poly-N vinyl 5 ethyl-2-oxazolidinone (PVO-E). These species of the ring substituted N-vinyl- 2-oxazolidinone polymers are respectively depicted in the following structural representations:

wherein n has the above described value. Most advantageously, PVO-M is employed as the ring substituted N-vinyl-Z-oxazolidinone polymer. Of course, 4-substituted polymers may also be utilized, as may 4,5-substituted, 5,5-substituted, 4,4-substituted, and so forth. Both PVO-M and PVO-E, as well as other of the ring substituted N-vinyl-Z-oxazolidinone polymers that may be utilized in the practice of the present invention have been disclosed and described in the referred-to copending parent application Serial Number 696,317.

The hair setting formulations may have any desired concentration of the ring substituted N-vinyl-2-oxazolidinone polymer therein. Generally, however, it is of greatest economy to use less than about 5 percent by weight of the polymer as an upper limit despite the fact that, theoretically, no true upper limit exists. Better results are also obtained when at least about 0.5 percent by Weight of the polymer is incorporated in the composition. As indicated, the polymer is dispersed in a solvent carrier therefore which, of course, must neither be injurious nor in any way deleterious to the hair intended to be set during its contact therewith. The particular solvent employed depends upon the ring substituted N-vinyl-2-oxazolidinone polymer or mixture thereof being employed. Thus, PVO-M may be dispersed in water or in such aqueous carriers as mixtures of water and 1 to 4 carbon atom lower alkyl alcohols containing enough water (usually at least about 70 weight percent) to ensure solubility of the polymer. PVO-E, being water-insoluble, may advantageously be employed in an alcoholic carrier such as a water-alcohol mixture or, preferably, in an alcohol of the aforementioned type.

The compositions of the present invention may be applied to water-wetted or dry hair and spread therethrough by manipulation with the fingers or by combing so that the hair is thoroughly wet with the solution. Alternatively, and with equal advantage, the setting compositions can be applied to the hair by daubing or spraying techniques. After such application, the hair is arranged to give a desired configuration in any desired manner so as to achieve a suitable coiffure. Pin curls or curlers may be employed to achieve a pre-arranged pattern. The compositions of the present invention generally facilitate arrangement of the hair being set and tend to cause it to remain relaxed in practically any shape imparted thereto. If desired, the compositions may be applied to already arranged or configured hair, although such manner of practice may not be as flexible or as completely satisfactory from an aesthetic point of view.

After application of the composition, the set hair is dried in the so-called cold manner of operation wherein either open air drying (at room temperature) or term peratures not in excess of about 160 F., preferably less than 130 F., are utilized.

In many cases, especially when PVO-M compositions are being formulated, it may be particularly advantageous and especially desirable to incorporate various swelling agents with the polymer in the setting compositions. To this end it is of great benefit to utilize the same agents for the same general purposes and the accomplishment of the same type of results as are disclosed and indicated in the referred-to US. Patent No. 2,793,980. Thus, the compositions may be prepared with a ring substituted N- vinyl-2-oxazolidinone polymer, especially PVO-M, in place of the PVP and with lesser respective quantities of triethanolamine and urea being incorporated therewith. Generally, amounts of the triethanolamine and urea that are each from about one-half to about three-quarters of the weight of the polymer in the composition may be used with advantage. When such triethanolamine and urea-containing compositions are prepared, it is desirable for their pH to be from about 9 to 10.5 or so, as may be effected primarily by the concentration of the triethanolamine. Of course, equivalent swelling agents and hair swelling systems may also be employed.

It is also beneficial for the Fikentscher K-value of the ring substituted N-vinyl-Z-oxazolidinone polymers used in hair swelling compositions, such as those indicated, to be between about 15 and 40 to permit their easier penetration into the individual hair strands. If desired, however, polymers of lesser and greater K-values, say from 5-10 or lower to or higher, may also be employed in the practice of the invention. Suitably, various glossing and/or softening agents, such as the various lanolin and silicone compounds known to be adapted for such purposes, may also be incorporated in conventional and effective amounts in the compositions of the present invention in order to further benefit them in the indicated particulars.

In order to further illustrate without limiting the invention, the following examples are given.

Example A"- A blank hair setting solution (prepared for comparative control purposes) was made up with about 95 parts by weight of distilled water, 1% parts by weight of urea and 1 /4 parts by weight of triethanolamine. A PVP composition was made up from a polymer having a Fikentscher Kvalue of about 30, using the same ingredients as in the blank with the addition thereto of about 2 /2 parts by weight of the PVP. A PVO-M composition was similarly made up from a K-2l.8 polymer using the same ingredients as in the blank with about 2 /2 parts of the PVO-M being incorporated therein.

Several nearly identical locks of natural straight gray human hair were then prepared. Each lock was about eight inches in length. The locks were then Washed thoroughly in an aqueous detergent solution, rinsed thoroughly with distilled water and dried for 30 minutes at 122 F. Each dried lock was then found to Weigh about 2 grams. Separate locks were then individually immersed in each of the three prepared setting compositions for about 10 seconds. The excess solution was allowed to drip ofi of the test locks after their withdrawal from the compositions. Each of the treated locks was then made into curls using identical, conventional, commercially available hair curlers for the purpose. Each of the curls was then dried in an oven at 122 F. for about 90 minutes. They were then mounted on a horizontal rod at equal heights. An inch scale card was placed behind the curls in order to obtain a measure of the curl fall out. The curlers were then removed from the curls and a glass rod used to uncurl them, after which they were each permitted to spring back naturally. By use of the scale and a timer, the rate of curl fall out of each of the treated curls Was determined at various relative humidities (RH) and temperatures. The results are set forth in the following tabulation:

Minutes/inch (1) At 25 percent RH and 78 F.:

(a) Blank w 150 (b) PVP (c) PVO-M 260 (2) At 60 percent RH and 89 F.:

(a) Blank 8 (b) PVP 14 (c) PVO-M 4-7 (3) At 77 percent RH and 93 F.

(a) Blank 15 minutes to complete curl fall out. (b) PVP 5 minutes to complete curl fall out.

(0) PVOM Not completely out in 30 minutes.

The percent by weight of polymer pick up on the hair for the above tests was found to be about 2 percent for the PVP treated locks and about 3.1 percent for those treated with PVO-M.

The foregoing procedure was then identically repeated with additional test locks of the same type excepting to immerse the lock in both the PVP and PVO-M compositions until about identical 4.4 percent by weight pick ups were achieved. At 21 percent RH and 72 F., the rate of curl fall out was as follows:

(4a) Blank 400 minutes/inch. (4b) PVP No change in 480 minutes. (40) PVO-M No change in 480 minutes.

In each of the foregoing tests, the PVO-M treated locks felt appreciably softer (even when higher pick ups were involved) than those to which the PVP had been applied. No odor whatever was detectable in the hair treated with PVO-M, even when checked at a considerable period after the treatment. The PVO-M also evidenced greater aflinity for hair than PVP, as is apparent in the foregoing data.

Example B PVO-E having a Fikentscher K-value of about 16.4 was prepared into a formulation of the following composition suitable for use with an aerosol dispenser:

The formulation, after being prepared, was placed in an aerosol bomb type of dispenser of the conventional variety. It was then employed to spray natural human hair of a gray color. Two locks of hair were made up. Both were washed with water. One lock was set with a hair curler while wet; the other was sprayed for about five to ten seconds at a distance of about 18 inches with the PVO-E-containing formulation, then set with a curler. After drying, the PVO-E-sprayed lock was found to be free of any tackiness. After two hours, the curlers were removed. Both locks of hair were observed to have formed into good tight curls. The PVO-E- treated curl, however, was springy and remained wellformed for a considerable period (at least 48 hours) after the water-made curl had fallen out, which occurred within a period of time of about 4 hours.

What is claimed is:

1. A composition for setting hair comprising a ring substituted N-vinyl-Z-oxazolidinone polymer of the structural formula:

wherein each X is independently selected from the group consisting of hydrogen and alkyl radicals containing from 1 to about 4 carbon atoms with the limitation that at least one of said substituents is an alkyl radical, and n is a whole number of average value from about 10 to about 5000, said polymer being dispersedin a solvent therefor that is selected from the group consisting of water, lower alkyl alcohols containing from 1 to 4 carbon atoms and their mixtures.

2. The composition of claim 1, containing from about 1 to about 5 weight percent of said polymer.

3. The composition of claim 1, wherein said polymer is poly-N-vinyl-S-methyl-2-oxazolidinone.

4. The composition of claim 1, wherein said polymer is poly-N-vinyl-S-methyl-Z-oxazolidinone and said solvent is an aqueous solvent for said polymer.

5. The composition of claim 1, wherein said polymer is poly-N-vinyl-S-ethyl-2-oxazolidinone and said solvent is comprised of ethanol.

6. An alkaline composition for setting hair comprised essentially of a polymer of the Formula I, a solvent carrier therefor that is selected from the group consisting of water, lower alkyl alcohols containing from 1 to 4 carbon atoms and their mixtures, urea and triethanolamine.

7. An alkaline composition for setting hair comprised essentially of an aqueous carrier, poly-N-vinyl-5-methyl- 2-oxazolidinone, urea and triethanol-amine.

8. An alkaline composition for setting hair comprised essentially of an aqueous solution of poly-N-vinyl-S- methyl-Z-oxazolidinone in an amount between about 1 and 5 percent by weight, based upon the weight of the' composition, and urea and tn'ethanol-amine in respective amounts of between about 50 and percent by weight each, based on the weight of the polymer in the composition.

9. The composition of claim 8, whereinsaid poly N- vinyl-5-methyl-2-oxazolidinone has a Fikentscher K-value between about 15 and 40.

1 0. The composition of claim 8 having a pH between 7 about 9 and 10.5. V

11. An alkaline composition for setting hair comprised essentially of an aqueous carrier, poly-N-vinyl-i methyl-Z-oxazolidinone, urea and triethanolamine; said composition being further characterized inhaving a pH between about 9 and 10.5.

12. -A process for cold setting hair on the human head ing an aqueous carrier, poly-N-vinyl-S-methyl-2-oxazolidinone, urea and triethanolamine.

' References Cited in the file of this patent UNITED STATES PATENTS 2,793,980 Mamlok May 28, 1957 2,818,362

human head Drechsel Dec. 31, 1957 

1. A COMPOSITION FOR SETTING HAIR COMPRISING A RING SUBSTITUTED N-VINYL-2-OXAZOLIDINONE POLYMER OF THE STRUCTURAL FORMULA: 